DE2058201A1 - 4-butyl-2,6-dinitroanilines, processes for their preparation and their use - Google Patents

Description

J | -Butyl-2,6-dinitroaniline, process see below their division as well as their use

The invention relates to certain 4-butyl-2,6-dinitroanilines and their derivatives, the subject matter of the invention in particular being single compounds which have berbiside properties.

Many 2,6-dinitroanilines are already known and swar both for their herbicidal activity and for other reasons such as their use as fungiaids.

US Pat. No. 3,119,736, for example, describes compounds of the general formula I.

(I)

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in which R is a hydrogen atom or a lower alkyl or Aoyl radical, R a hydrogen atom or a lower alkyl radical, W and X are halogen or nitro, alkyl or alkoxy, and Y and Z are hydrogen Are halogen or nitrogen, provided that at least a nitro group is present, but at most the groups W, X, Y and Z are nitro groups, are valuable fungicides, with Emphasizes that a number of compounds which include 2,4-dinitroaniline, 2,4,6-trinitroaniline and i-methyl-2-nitroaniline belong, special are valuable. Corresponding patents are the British patent 84 * »916, the French patent 1 217 677 and the German patent 1 108 975

From US Pat. No. 3,257,190 it can be seen that compounds of the general formulas II or Ha

NO,

(II)

NO.

(Ha)

in which R is a Wasseretoffaton, a lower alkoxy or by lower alkylreet ditubatituated carbamyl radical,

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R ₁ "in a lower alkyl radical" has 1 to 3 carbon atoms, a cyano radical, a halogen-substituted lower alkyl radical or a halogen atom, R ₂ an ethyl, n-propyl, n-butyl, sec-butyl, iso-butyl or by a lower alkoxy group substituted lower alkylreet and R, and R ^ each for eich C ₁ -C ₅ -IUqTl-, C ₂ -C _$ -alkenyl-, Cg-Cj-alkynyl-, substituted by lower alkoxy groups or lower alkyl ■ with lower alkoxy groups are disubstituted lower alkyl radicals or R ₂ and R- as well as R, and R ^ in each case seeds ■ it the "nitrogen atom" to which they are bonded form a pyrrolidine or piperidine radical, although the restriction applies because »The buttocks of the carbon atoms in the hydrocarbon chains of R ₂ and R. susanaen and R. and R ^ susaaaen are less than 9 iat, suitable, among other things, to prevent the formation of seeds and sags in grasses and at the same time serve to selectively destroy broad-leaved weeds can. Some precautionary compounds are N, N-Di- «ethyl-2,6-ilinitro-e-toluidine, Μ, Ν-Di-sec. -butyl-4-triflor- «ethyl-2,6-dinitroaniline and Ν, η-propyl-N-tert-butyl-2,6-dinitro-p-toluidine

Similar connections are in the German Auslegesohrift 1 300 727, from which it follows that compounds of the alIge — ine »forael ZIZ

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20582Q1

(III)

in which R is an n-alkyl radical with 2 to 4 carbon atoms or the allyl radical, R * is an n-alkyl radical with 1 to 1 carbon atoms or the allyl radical, and R "is a hydrogen atom, a halogen atom, the trifluoromethyl radical or an alkyl radical with 1 to * carbon atoms or R and R * together with the nitrogen atom form a piperidine or pyrrolidine ring, provided that "R" is not a hydrogen atom, are valuable selective herbicides. Some particularly preferred compounds are N, N-Oi-n-propyl-4-tert-butyl-2,6-dinitroanal and N _t M-di-n-propyl- ^| l-seo.-butyl-2,6-dinitroaniline.

The JMA patent pen 3 332 769 describes that "connections of the general formula XV

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20582Qt

(IV)

in which R is a hydrogen atom, a C ₁ -Ci-AHqTlTeSt (sB a methyl- »Xthyl-, n-propyl or iso-propyl radical), a Hslogenatoa (sB a chlorine, Bro« - or Fluoratoa) or a C ^ -C.-haloalkyl radical (eg a trichlonsethyl radical, an iodo- ethyl radical »a bromethyl radical, a pentafluorophyl radical, a heptafluoro-n-propyl radical, a heptafluoro-iso-propyl radical or a trifluonic ethyl radical) and" all "is a secondary C ₃ -C ₇ -Alkyl radical without quaternary carbon atoms means “valuable herbicides are” where N- (sec-butyl) -2,6-dinitro-n-fluoro-aniline, N- (2-beptyl) -2 _f 6-dinltro-p-toluidine and N- (4-methyl-2-pentyl) -2,6-dinitro-4-ithyl aniline are particularly useful. Corresponding patents are British patent specification 1,071,478 and French patent specification 1,515,830.

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Sohlirtlieh emerges from the VSA-Patenttehrift 3 ** »9 ill, daft connections of the general PonMl V

(V)

in the R tin hydrogen atom, "in Cj-Cj-Alkylreat, a halogen atoa ait" in * * atomic weight below 85 "a halogen-substituted Cj-C.-Alkyir · t with a Halogenatoa nit 'an atomic weight below 85, a Cj- C. _t Alkyleulfonylreet a Sulfonanidrest or Cyanreet 1st and R ¹ and R ^{2 are} either the same or comparable • ohieden IN4 and a Xthyl-, η-butyl or n-Propylreet mean la lonblnation nit beetiamten Allcyl-NN-dUlkylthiolo & rbemten in fleeing nit flansen are valuable · herbicides are. Particularly avoided compounds of the general Pomel V are N, N-di-n-propy 1-2,6-dinltroaniline and », N

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-T-

Such 2,6-dinitroanilines are found in a variety of ways as Herbisides Application and some · have become economically significant. In general, the 2,6-dinitroanilines Oraser and Destroy brittle-leaved plants which are in sewer ditches occur on gravel paths, roadsides or in trees. 31 · are still suitable for wiping old herbiides the Purohs in Hai · - * »cotton or soybean fields, in Blackberry plantings or similar areas old grooved walls, Vorauagesetst, which can be applied in a solo way, because * al · do not reach the groove flanks. You can also al · pre-emergence herbicide time of sowing, for example Maie »Bauawolle» Soybeans, Wise Men, Sugar Beets and such as be valuable. When used in this way, the 2,6-dinitroanilines destroy the budding weeds without the germination and growth of the grooved walls.

Su the 2,6-Dinltroanilinderivaten found in practice belong daa eC, <£, <£ - trifluoro-2,6-dinitro-N, N-dlpropvl-p-toluldin (also, known ala trifluralin) and daa * - («ethylsulfonyl-2,6-dinitro-H, ll-dipropyl-aniline (also known as litralin); the ·· two connections are found as Pre-emergence berbiside for cotton, soybean, dry Beans, sugar beets, peas and other nut plant uses.

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At the· . often used for weed control in the Farmer recommended special 2,6-dinitroaniline derivatives • ind among other things 2,6-dinitroaniline itself and its N-Xthyl- and N-n-propyl derivatives such as 2,6-dinitro-p-toluidine and its N, N, -di-n-propyl and -dlally 1 derivatives. Connections of these Art are for example in the above-mentioned patents mentioned.

Trots the good herbal activity of these 2,6-dinitroaniline derivatives None of these are completely satisfactory in every respect. Some of them are broad and general It is expensive to use, as it can only be obtained with the help of complex syntheses which require several steps and give relatively low yields during manufacture other via unstable nitro compounds, the handling of which is dangerous; still others of these connections, which have been recommended as herbisides are actually not sufficiently selective as they are often too the grooves damage, even if careful attention is paid to the connections in the lowest, barely effective Apply dose and also exclude direct contact with the groove wall.

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Generally speaking, it can be stated that the most economically strong 2,6-dinitroaniline derivatives are N, N-disubstituted compounds, in particular solos, which as a functional group are not an alkyl radical, but, for example, a halogen atom, a haloalkyl radical, a methylsulfonyl radical or the like in the p-position su have the asdno group. Of the known M, M-disubstituted compounds of this type, the methyl compounds Ia have generally proven to be more effective than the higher alkyl compounds, such as the propyl or butyl derivatives. Oeageaäss have check the researchers to date the 2,6-dinitro sugewandt _f which in p-3teilung another functional group as an alkyl - or head not funktlonellen radical - having, and as far as alkali metal compounds have been investigated, the compounds were ait based on previous experience of the toughest carbon chain. In Ihnllober Velse, in the case of substituents on the Stiekstoffatoa, the disubstituted compounds have been avoided over the aonoubstituted ones.

Now it was found that ait defies previous experience N, H-disubstituted compounds (in which an Zunaiwe der OrOIe of the alkyl substituent in the p-position the herbiside Effectively reduced) certain ■ ono-N-substituted 4-Butyl-2,6-dinltroaniline a particularly high herbiside

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Have effectiveness and a particularly good selectivity compared to various agriculturally important grooved walls exhibit. The N-mono-alkyl derivatives, especially the N-propyl and N-butyl compounds and in particular the Ieopropylr, gee.-butyl-'tert.-butyl compounds have proven to be both hinsiohtlioh of weed killing as auoh of security highlighted as unusually effective herbicide for the hat flans. Di · horbiside effectiveness of the N-monosubstituted Compounds according to the invention is particularly surprising when one them with the effectiveness of the corresponding Ν, Ν-disubstituted Compares connections. For example, it has been found that ft-tert-butyl-N-seo.-butyl-ZyS-dinitroaniline is unique has selective berbiside properties »while the corresponding Vtert ~ butyl-M, N-di (eeo.-butyl) -2,6-dinitroaniline as selective herbicide is not nearly as effective.

* It is particularly surprising that none of these H-Buty 1-2,6-dinitroanilines so far in the literature - either in general still spesiell - has been described if one dl · fact Consider that these compounds have now been discovered Most effective · Herbisides are, which are by means of a can be produced in a convenient synthetic process and only one when used as herbicide on grooved wood minimal or essentially no sohädllohen

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B Effect, How Can Be Detected ·.

eegenatand of the invention "in" thus once mono-H-aubatituated 4-Butyl-2,6-41nitroanlline d # r general phone ·! VI

(VI)

MR

in the Bu · 1η · η tert-butyl- or aee.-Butylreat b «d« ut «t and R« in vaaeratoffatom or «in Alkylreat, a Cycloalkylreefc,« in Cyoloalkylalkylr «« t ₉ «in Alk« n / lr «et,« in alkynylre »t,« in alkoxyalkylr «et or« in dialkoxyalkyl radical, as well as their Bali ·. The acrolreat R can be a straight or branched alkyl reet, which presumably removes 1 to 6 carbon atoms, so it has a methyl, ethyl, n-propyl, iao-propyl-, η-butyl · ^ aeo.-butyl -, tart.-Butyl-, n-Avyl-, aeo.-Aayl-, Hexylreat or the like, in particular a Reat adt 3 bla 6 carbon atoms «The iao-propyl, seo-butyl and tert-butyl groups are especially precautionary.

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The Cyoloalkylreet R is favorably monocyclic and advantageously contains 3 to 6 coals hot it is eloh ε.B. a cyclopropyl, cyclobutyl, Cyolopentyl or Cyolohexylrest, the latter especially is precautionary.

The cyoloalkylalkyl radical R preferably contains a total of k to 9 carbon atoms; eB is a Cyclopropylmethy1-, Cyelobutyläthyl-, Cyclohexylpropyl- or precaution a Cyolohexylmethylrest.

The alkenyl radical R can be straight or branched chain Alkenyl radical, r.B. an allyl, 2-butenyl, 3-butenyl, pentenyl, Hexenyl radical or a similar group, but preferably a residue of 3 or 4 carbon atoms, the allyl residue being avoided.

The Alkynylreet R can be a straight or branched-chain alkynyl radical, for example a propynyl, 2-butynyl, 3-butynyl or fentynyl radical, preferably a radical with 3 or H carbon atoms, preferably a propynyl radical.

Alkoxyalkyl radical R is conveniently a radical of the general formula CH, (CH ₂ ) _a -0- (CH ₂ ) _n -, in which m is O or 1 and

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- 13 -

η ein · gansa number from 1 to 6 iat; Examples of such The remainder are Kethoxyaethyl-, Methoxyäthyl-, Methoxypropyl-, Methoxyisopropyl, xthoxyaethyl, xthoxylthyl, Xthoxypropyl and Xthoxyieopropylreete.

The Oialkoxyalkylreat R iat advantageously a radical

the general formula i ^CH 3 < ^CH 2 ^ _B ~ ° ^ 2 "" ^C n ^H 2n-l ~ ' ^{in which n} and η have the meanings given above; Examples include diaethoxyethyl, dinethoxyethyl, ethoxypropyl, diaethoxyisopropyl, dittnoxymethyl, dietoxyethyl, diIthoxypropyl and Dilthoxyisopropyl radicals.

Ia Rabaen represent compounds falling under the common Foraal VI is a preventive group arfindungagaalaa the one in the case of Dar Dar heat bu ain tert-butyl creat iate »and in particular Jana connections, bai danan the subatituent R ain alkyl radical iat.

Pia especially precautionary connections in general Foraal VI are Jana, in which the remainder Bu is a tert-butyl residue and the substituent R is a branched-chain alkyl radical, in particular ain sec-butyl or iso-propyl radical.

Baispiala for spasialla particularly preferred connections gaalaa invention are the following, with the Soheelt-

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- i4 -

4-tert-butyl-N-methyl-2,6-dinitronailine (129-130 ° C); 4-tert-butyl-N-ethyl-2,6-dinitroaniline (70-73 ⁰ C); 4-tert-butyl-N-ieopropyl-2,6-dinitroaniline (71-73 ° C); 4-tert-butyl-N- (n-butyl) -2,6-dinitroaniline (63-65 ⁰ C); 4-tert-butyl-N- (aec-butyl) -2,6-dinitroaniline (60-62 ° C); 4-tert-butyl-N- (tert-butyl) -2,6-dinitroaniline (81-83 ⁰ C); 4-tert-butyl-N- (tert-pentyl) -2,6-dinitroaniline (49-56 ° C); 4-tert-butyl-N-isopenty1-2,6-dinitroaniline (38-4O ° C); -tert-butyi-N-allyl-2,6-dinitroaniline (56-58 ° C); -tert-Butyl-N- (3'-nethoxypropyl) -2,6-dinitroaniline

point in Klaanern is given:

-tert-butyl-M- (2 * , 2 '* dimethoxyethyl) -2,6-dinitroaniline

(dark organic liquid);

-tert-butyl-N-oyolohexy1-2,6-dinitroaniline (89-90 ° C); -tert-butyl-M-n-hexyl-2,6-dinitroaniline (liquid); -tert-butyl-N-oyolopropy1-2,6-dinitroaniline (125-126.5 ° C); -tert.-Buty1-K-cyclopropylaethy1) -2,6-dinitroaniline (-);

-see.-Butyl-N-methyl-2,6-dinitroaniline

(dark organic liquid);

-see.-butyl-N-ethyl-2,6-dinitroaniline (44-45 ⁰ C); -see.-Butyl-N-ieopropyl-2,6-dinitroaniline (semi-solid); -see.-Butyl-N-seo.-buty1-2,6-dinitroaniline ■

(dark organic body);

-see.-Butyl-N- (n-butyl) -2,6-dinitroaniline (liquid); -sea-butyl-N- (tert-butyl) -2,6-dinitroaniline (33-38 ° C); -see.-butyl-N-oyolohexy1-2,6-dinitroaniline (65-67 ⁰ C); -eec-butyl-N- (2 ·, 2 · diwethoxyethyl) -2,6-dinitroaniline

(liquid) i

(24) 4-seo-butyl-N- (3'-methoxypi

-2,6-dinitroaniline

(fluid).

The Bono-N-tubstitulertin 4-butyl-2,6-dlnitroaniline · g «« eat Invention can be made to any suitable size.

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However, they are preferably obtained by means of a process in which a corresponding primary amine RNH ₂ (where R has the meaning given above) with a suitable H-butyl-2,6-dinitrophenyl chloride of the general formula VII

(VII)

is converted »where Bu also has the meaning given above Has.

The amines mentioned are generally liquid and in the refuse inert organic solvents such as toluene, Xylene and ethanol soluble, which accordingly as the reaction medium Can be used. However, if the amine is water-soluble, an aqueous reaction medium, like s.B. aqueous * Xtbanol, apply. The tuetsung easily takes place if one dissolves the amine in the appropriate solvent and the phenyl chloride in the same Solvent drop ItAt, the amine being preferred in a «molar überereohu * is used. Naoh termination

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the addition, the mixture is heated to reflux until the The action is complete, based on the course of the reaction the formation of the hydrochloride of the unreacted amine can be observed that usually separates out as a solid precipitate, which precipitate is filtered off and the piltrate is concentrated to dryness. The solid residue is then advantageously made from an organic Recrystallized solvent, see B. from methanol or ethanol to obtain a pure product eu in this way.

The 4-butyl-2,6-dinitrophenyl chloride used as the starting material the general formula VII can be obtained in a simple manner from the corresponding p-butylphenol by means of the following reaction steps can be obtained:

a) The p-butyl phenol of the general formula IX

(IX)

OH

in which Bu has the meaning given above, it is preferably dissolved in acetic acid using nitric acid see the corresponding * -butyl-2,6-dinitrophenol of the general

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»A forum ·! VIII

(VIII)

nitrided. The nitration is carried out according to the procedure generally known for the nitration of pbenols, as was also the case results from the following examples in one.

b) Dae obtained in this way is 4-butyl-2,6-dinitrophenol then into the corresponding 4-butyl-2,6-dinitrophenyl chloride of the general formula VII

(VII)

^{flb # r} leads. This conversion, which is the decisive step for obtaining the compounds according to the invention, is achieved using a chlorinating agent such as thionyl chloride, phosphorus oxychloride or phosphorus penta chloride in the presence of one of the complexing agents described below. Such

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Chlorinating agents are known per se, although the conditions used here are not the usual ones Are reaction conditions.

The chlorination is usually carried out by treating the as Starting material used phenol achieved with a chlorinating agent in an inert solvent. For example 5-tert-Butyl-2,4-dinitrochlorobensol from p- (tert-butyl) aniline obtained by acetylation, chlorination, Sandmeyer reaction and nitration (Capon * Chapman, J.Chem.Soe. 1957, P. 6 * 00). Another example is the synthesis of 6-tert-butyl-2, * - dinitrochlorobenzene mentioned, which by nitrating the 2-tert.-butylphenols, methylating the resulting dinitroderivate, Conversion of the methoxy compound into the AmIn and sohlieslioh Diasotierung and Sandmeyer reaction carried out (Chemical Abstracts 50, 11260b).

It has now been found that the chlorination of i-butyl-2,6-dinitrophenol can be carried out by using one of the above-mentioned chlorinating agents as the chlorinating agent with an · «amide, such as formamide, acetamide, proplonamide or their alkylated derivatives,« such as dimethylformamide, used The chlorinating agent and the amide are preventative Singesetst in approximately equimolar amounts, obgleioh that

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20582Ö1 - 19 -

Chlorinating agent can be present in a "top hat"; in any case the acetamide and the chlorinating agent should normally both be present in solar amounts equal to the amount of 4-butyl-2,6-dinitrophenol equal or better than this.

The conversion is carried out in a convenient manner in an inert organic Solvent, such as toluene or xylene, carried out and the reaction temperature is conveniently the return air temperature the reaction mixture (usually about 110 to 120 ° C), although higher or lower temperatures with correspondingly shorter or longer reaction sides can be used. The reaction is normally complete in about 12 to 16 hours, so that the excess chlorinating agent is then used from the reaction mixture can be stripped off, however, under reduced pressure at about 30 mm. The desired chlorinated compound remains surttok in the upper liquid phase, while the chlorinating agent and the amide (as Complex) see depositing as a heavier liquid layer and accordingly can be easily separated from the top layer.

The chlorinated product obtained in this way can be precipitated from an inert organic solvent such as η-hexane the pure 4-butyl-2,6-dinitrophenyl chloride is obtained in high yield for the process according to the invention Can be used.

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The mono-N-substituted i-butyl-2,6-dinitroanilines can also be used according to the invention, if necessary, also through Treatment of general butyl-2,6-dinitrophenols Forsei VIII with p-toluenesulfonic acid or methyltoluenesulfonelure or a similar means like the known methods to introduce a tosyl, meeyl or similar Sobutsrestes are treated. The corresponding toaylat or a similar derivative can be modified in a known manner.

The mono-N-substituted * l-butyl-2 _f 6-dinitroanilines according to the invention have an extremely interesting herbicidal activity, so that they can be used for the extermination of weeds, in particular for selective extermination. The invention accordingly furthermore relates to the use of the mono-N-substituted 4-butyl-2,6-dinitroanilines according to the general formula VI or their salts for regulating the growth of undesired vegetation, in particular for controlling weeds.

The compounds according to the invention are obviously sur Destruction of seedlings and seedlings of weed grasses and broad-leaved weed species as well as stimulation suitable for the growth of certain fflans. In particular aind

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they but selective inhibition of the growth of unwanted grasses and broad-leaved weeds in fields with agricultural crops Useful plants as well as for the simultaneous promotion of the growth of the grooved walls. Above all, can Weed grasses and broad-leaved weeds on cultivated areas by pre-emergence application, preferably by application sowing on areas which are suitable for cultivation with corn, beans, potatoes, cotton, sorghum, tomatoes, asparagus, Onions, pumpkins, grains, beans, beets, pepper, sunflowers and similar species are prepared to be destroyed.

A particular advantage of using the inventive Compounds is that the growth of Nutspflansen with a dosage of the compounds, which to curb the Weeds is sufficient, is not adversely affected. These compounds and in particular 4-tert-butyl-N- (sec-butyl) -2,6-dlnitroanlline have sioh opposite ourken, watermelon and squash, beans, such as soybeans, and dry beans Other beans, corn, sorghum and potatoes have proven to be particularly safe. The surprisingly large distance from 3.3 to 6.6 kg / ha and above between the dose sufficient to destroy the weeds and the dose at which a still permissible dose Damage to the groove flanks occurs, is particularly noteworthy if one compares the known 2,6-nitroaniline

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sees, which in general can only be used if "accepts considerable damage to the useful plants, UB the inner even greater advantages of weed killing reach. During field tests with Qurken, Maie and Areas planted with potatoes show abundant and vigorous growth of the nut plants after treatment with quantities of the plants according to the invention ) Compound sufficient to stop the germination and growth of most common weed species. These Ability of the connections according to the invention to prevent the growth of a wide range of Qrasweeds and broad-leaved weeds with simultaneous vigorous growth of the crop species is also derived from the following experimental results.

The application dose for the compounds according to the invention varies between 0.28 and 17.6 kg / ha, the application either as a pre-emergent herbicide on the soil during the Order or by placing it in the ground when ordering. Preferred application amounts depend of course depends on the type of grooved plant and the type of area being treated, although usually one effective control of weeds without damaging crops such as maize, potatoes, soybeans, cucumbers or melons, can be achieved by using the compounds according to the invention

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used in amounts of 0.55 to 5.5 kg / ba. The inventions Compounds have also shown some herbicidal activity in water, making them replanted as pre-emergent pests Can be used in rice fields »

In addition, the compounds have found utility as plant growth regulators proven when used against tobacco plants or similar species.

Before using any of the compounds according to the invention but weed control they are preventively with a agriculturally suitable carrier processed su an appropriate mixture. The invention therefore relates to eventually means eur inhibition or regulation of the Pflansenwaohstums, which one or more of the compounds according to the invention contain susans with an agriculturally suitable carrier.

The compounds according to the invention can be conveniently used as pre-emergent herbicide either in the form of liquid or from granular compositions, which as a precautionary measure to be incorporated into the soil during the ordering process. The compounds are mostly crystalline substances with only low solubility in water, so that when liquid compositions are to be prepared, they are in the form

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wettable powder or emulsifiable concentrate application which can easily be tiled with water before application. The links can also be found in fora by Herbitid dust preparations find application, welohe if necessary sdt fertilizers or with other herbaceous such as N, M-dialkylthioloarbamates, can be combined. Suitable Granulated Susaamensetungen allow you to dissolve easily of the active ingredient converted into a "light organic Solvents such as i.B. Acetone, and spraying the solution on a carrier such as attapulgite, clay or vermiculite, if «evaporates after the solvent. Such granules, and in particular 4-tert-butyl-N- (eee. ~ Oranulates containing butyl) -2,6-dinitroanlline are special suitable Vbrauflaufverniohtunealttel against Digitarla • to «* inalie. The invention therefore particularly relates to granulated lussmmsnsetsungon with a novel compound according to the invention and a granular carrier material, which optionally can also be a fertilizer such as ammonium nitrate, granular urea, etc. Suitable granulates are those the approximately 2 to 20 Oew * of the active ingredient equally on a robust carrier material, such as attapulgi ^ clay, Contains vermiculite or ground corn on the cob. These oranges have been found to be particularly suitable for

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proven to be used in turfgrass by sewing dlgltaria, as shown in the test results given below.

Miscible consentrates can be made by using the herbal compound in an organic solvent, see B. an aromatic oil that is dispersible in water solves and optionally one or more solubilizers like s.B. higher alcohols or ketones or butyrolaoetone susetst. Such consentrates are preferably made with wetting agents, any suitable wetting agent, the means both anionic, cationic and nonionic can be used.

The novel dinitroaniline derivatives according to the invention can optionally be combined or combined with others known Herbisiden use. In particular, see combinations of 4-tertrBtity 1-N- (see.-Butyl) -2,6-dinitroaniline and EPTO (S-ethyldipropylthiocarbamate) as Proven to be effective, especially precautionary when treating potatoes before setting them. The invention is therefore particular also on the use of the new compounds, in particular 4-terVbutyl-N- (seo.-butyl) -2,6-dinitroaniline robbed in connection with one or more known Herbisiden, whereby each part of a connection is misled

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Invention also about 0.25 to * .0 weight parts a ·· known Herbitids, such as chloramben, BPTC and others are used will. The combinations are normally used in such amounts that the compounds according to the invention in at a dose of 1.1 to 2.2 kg / ha.

As shown below, the compounds are according to Invention, in particular the * l-tert-butyl-N- (eec.-butyl) -2,6-dinitroanllin, opposite to rice sioher and you can next to that Application before planting in certain pills also as a pre-emergence herbicide in replanted rice fields Find. In this case, as in the case of application before planting, the compounds according to the invention are inherent in comparison to those known below Dinltroaniline Herbisiden a remarkably lower one Perslstens in the ground; this will make them in terms of dat absence of unwanted residue more usable.

The compounds according to the invention show up when used Plants, such as tobacco and thinning species, also have a plant growth regulating activity. lur influencing The new compounds are de · waehstuma of tobacco profiles According to the invention after the decapitation of the tobacco plants applied, and twar vorsugswelse on the Stammbereioh of

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Tobacco plant, which of course achieved in a convenient way «Can earth, meanwhile« sprayed on the whole plant. The plants according to the invention are placed on the decapitated tobacco plants suitably by spraying with a dose of 1.1 to 6.6 kg / ha and in particular about 2.2 kg per ha preventive care in combination with a suitable surface-active agent Fabric in a henge swiscben about 0.05 and 2 ows, lied to the active ingredient, bandaged. The compound avoided is 4-tert-butyl - * - (seo-butyl) -2,6-dinitroaniline and the combination of this compound «it de« surface-active Medium is preferably about 472 to 1890 liters / ha of water applied by spraying. Suitable surface-active agents are the ionic or non-ionic (especially the last) surfactants, which are commonly used in herbicidal compositions. Examples of anionic surface-active agents are the sulfonates (See, for example, the alkylbenzene sulfonates), the sulfated surface-active substances Medium (e.g. sulfated alcohols, acids, amides, Esters and sulfated natural fats and oils) and the Phosphate esters (see e.g. the alkyl polyphosphates). Suitable non-ionic Substances are the polyoxyethylene compounds (see B. thoxylated alkylphenols and ethoxylated aliphatic alcohols) and the carboxylic acid esters (see e.g. polyethylene glycol esters and polyoxyethylene fatty acid esters ).

109827/2279

The particularly preferred compound according to the invention is 4-tert-butyl-N- (eec-butyl) -2,6-dinitroaniline. This compound in particular shows a growth-increasing effect on nut plants, especially cotton, beans (soybeans, dry beans and lima beans), potatoes, melons (see cantaloupe species and watermelons) and other types of pumpkin (see cucumber) and others. This effect is particularly noticeable in warmer climates, especially in areas where the soil temperature is generally around 15 ^° C. or above.

The effect of increasing the growth of crops by treatment with 4-tert.-butyl-N- (sec.-butyl) -2,6-dinitroaniline manifests itself as overall growth stimulation, which is greater than that which normally occurs as a result of the destruction of the competing species Weeds alone. is enough. i _n planted with H tert-butyl-N- (sec-butyl) -2,6-dinitroaniline treated soil useful plants show a stronger healthy growth, and a significant increase in yield compared with comparison samples in which the weeds by hand is removed; it has been shown that the increase in yield exceeds the effect normally achieved by eliminating the competition for nutrients that depends on the presence of undesirable

109822/2279

- 29 weeds are declining.

The mechanism by which the 4-tert-butyl-N- (seo.-butyl) -2,6-dinitroaniline in hat plants such as cotton, pumpkin, beans and the like "causes an increase in growth if it is used in a dose suitable for weeds such as Rleaenfoxtail (Alopecurus pratensis), Crabgrass (Digitaria aanguinalis), barnyard grass (Echinchloe crusgalli), Herbstpanicum, Ryegrass (Lolium temulentum) and others are toxic, cannot be fully explained. However, he allows himself in certain Cases on a physiological reaction of the plant or an elimination of one or more agroclmatic Attribute damage in other cases or to a combination of these two factors.

Agroclimatic damage is understood to mean those environmental factors which normally affect the seeds in the Act Erdreioh and a detrimental, if not toxic, effect on the germination of the seed and / or the Have growth of plants. Such factors include soil pills, bacteria, Nematods-n, and the like as well as other pmthogenic nouns which either use the Wurselwerk or the plant itself can attack and at the same time normal growth due to the weakening of the pea

109822/2279

or by disturbing the nutrient intake. Other factors are temperature, light quality (wavelength), the light duration (reaction of the plant to the days β-length) and the moisture.

The treatment with 4-tert-butyl-N- (sec-butyl) -t 2,6-dinitroaniline achieved growth stimulation shows not only in increased yields, but also in the "production" ▼ on plants that are harder and stronger and opposite Diseases and adverse climatic conditions are less sensitive. In addition, show with i-terfc-butyl-N- (seo.-butyl) -2,6-dinitroaniline treated plants do not form root knots as they are for treatment characteristic with the well-known 2,6-dinitroaniline herbicides is; the former causes an increased root development, especially with regard to the number, size and strength of the lateral roots. This at 4-ter $ .- butyl-N- (sec-butyl) -2,6-dinitroaniline observed effect of increased growth stimulation results from the field tests described below.

In addition to the advantages described above, the mono-N-substituted 4-butyl-2,6-dinitroaniline according to the invention and in particular 4-tert-butyl-H- (aec-butyl) -2,6-dinitroaniline

109822/2279

surprising and completely unexpected results, which so far could not be shown with any of the known dinitroaniline herbicides, 4-tert-butyl-N- (see-butyl) -2,6-dinitroaniline has proven to be particularly effective against Johnson grass (Sorghum halepense), a hibernating species and in this as well as other herbicidal uses it has been shown to be of value when it is used for weed control is used as early as autumn during the subsequent sowing or planting and growth period. For applications in In autumn it is of course desirable to use larger amounts, generally from about 3.3 to 13.2 kg / ha, depending on the type of weed infestation, soil type and other factors. When treating turf grass with a Means in orange form has been surprisingly cheaper Effect shown when the agent is used as a pre-emergence herbicide against Crabgrass (Oigitaria). In this case it has the granulate proved to be superior to a liquid preparation.

* -tert-butyl-N- (sec-butyl) -2,6-dinitroaniline has a wide safety margin between the dose causing damage to the crops and the doses at which a complete weed destruction can already be achieved. This is of particular importance when growing plants

109822/2279

for seed production where the small cultivated areas permit the use of high doses of herbicides of about 6.6 to 8.8 kg per hectare or more, that is to say of doses which usually used to treat common field crops are no longer economical. In this way the compound can find use to treat harmful weeds, in particular Oras, without damaging the grooved plants, completely destroy them. This large area of security allows about it in addition, the use of excessively large doses for the control of hard-to-kill weeds, such as Morning-glory (Ipomoea) and tea-herb, as well as black salmon and calf feet. When using this high dose During a growing season or two, weed populations on these difficult-to-control species be lowered to a level sufficient for several subsequent growing seasons with normal weed control for the crops is no longer detrimental.

4-tert-butyl-N- (aec-butyl) -2,6-dinitroaniline has proven to be particularly suitable sur control of weeds on areas where crops such as beans (e.g. soybeans, Lima beans, dry beans, French beans or green beans, pinto beans, kidney beans and the like), peanuts, tomatoes,

10982? /? 279

Pumpkins (see B. cucumbers, Hassers * ions, cantaloupes, honeydew melons or pumpkin melons), pepper, tobacco, rice (especially transplanted rice), potatoes, white or Irish potatoes, yams, safflower, sunflowers, castor beans, Okra, sugar beets (in this case, the application should be after the beets are 10 to 15 cm high or by bringing in before the beets are silted), sugar cane (application after tilling flat in the ground inside), cruolfers (such as cabbage, broccoli, cauliflower, winter cabbage, rapeseed, beetroot, mustard and rutabaga), umbilicus (such as carrots, radishes, dill, celery and parsley), turf grass and ornamental plants (especially perennial flowers, where the connection is introduced into the soil surrounding the ornamental plants) are cultivated. The connection can sur find weed control in orchards use by planting them in the ground, so that an excellent Weed control «wipe fruit and nut trees that are already standing. The compound is particularly effective sur control of grasses such as crabgrass (Digitaria * anguinalis), Foxtail (Alopeourus pratensis), Barnyardgrass (Bohinohloe orusgalli), Herbstpanicum, Johnson grass (Sorghum nalepense), Cheatgraes (Bromus seoallnus), Black grass (Alopeeurus), Braobiaria, red rice, witch grass, silver crab grass, blue grass (Poa annua), Ryegrass (LoIium temulentum) and many broad-

109822/2279

leafy weed species, such as pigweed (polygon »avioulare), Purslane, Florida pusley, Stellaria media, Atriplex, tea herb, Ipomoea, Koehia, Knotgrass (Polygunum avieulare) and many others.

This compound can be used to treat weeds, such as Sehwarsen Naehtsohatten and Teekraut, with dosages below Keep control or destroy, which for hat plants, like beans, act selectively, which is not the case with the well-known 2,6-dinitroanilines such as trifluralin and nitraline Is possible. This larger safety margin of the 4-tert. ~ Butyl-N- (seo.-butyl) -2,6-dinitroaniline, especially im Comparison to the analogous disubstituted compounds shows sioh from the following test results, which were obtained from field tests with the compound in comparison with other 2,6-dinitroanilines were obtained.

Herbiside efficacy and selectivity of 4-butyl-N-substituted 2,6-dilutroanlines

The tests leading to the results listed in Tables I to III below were carried out as follows: Tea fleas were made by mixing soil with fertilizer, sand and peat and being used for sowing, respectively Areas you used about 25 χ 50 cm and about 5 to 7.5 om depth.

109822/2279

The areas were arranged in rows with the species under investigation sown, covered the soil and watered until the soil felt damp. The test compound was tested on the Surface sprayed on before sowing and worked into the top layer of the soil of about 2.5 cm.

The results were assessed in comparison with the untreated Control areas, and were 4 to 5 weeks after sowing. the Prosentual effectiveness was assessed in the case of oras weeds and broad-leaved weeds on the basis of number and strength of the plants emerging on the treated areas compared with the untreated comparative areas. the corresponds to prosentual damage in the case of groove paws the AuemaA of the watch turn delay, which in comparison see below Groove flanking could be observed on treated soil and on untreated soil

In the tables, a "-" means that the corresponding examination was not carried out.

109827/7279

Table I 4-butyl-H-substituted 2,6-dinitroaniline derivatives of the formula VI

ο to oo

! SJ IN »

Bu
R. G. No, Stellaria media) t-bu
Me t-bu
Et t-bu
i-Pr t-bu
n-Bu t-bu
sec-Bu t-bu
t-bu Connection ia Avena fatura) 1 2 3 6th Dose leg "/ üntersuett »Plants rasa (Echinchloe eruagalli) 17.b 17.6 ö, ö ö.ö 8.8 0.0 Downy Brone (Bromus) AlopeeuruB pratensla) Chiekweed I Morning-glory (ii 10 100 100 60 100 100 Wildoat · ι YelTet-lea? TXbul O 100 100 30th 100 100 Barnyard pomoea, O 100 100 70 90 100 foxtail ι Silon] 10 100 100 75 100 100 15th 100 100 OO 100 100 Lncanum) O 15th 30th 0 85 0 Johnson grass (Sorghum halepense} 30th 10 25th 0 80 0 Pigweed (Polygonum aviculare) 10 100 100 f5 100 100 Laebe-quarter (Atriplex) 20th 100 100 Q5 100 90 Nutsedge 20th 100 100 100 95 Alopecurua 10 O 100 100 100 0 Curled dock (Ruoex crispue) 20th 100 100 100 100 Craberass (Dieltaria sanguinalia) O 100 95 95 40 50 30th 100 100 100 100 100

Table »I (port set)

Bu

t-Btt
tP

t-bu
i-Pe

t-Bu allyl

t-bu

■ tthoxy propyl

> ropyl

-Bu

t-bu

cyclohexyl

Connection no.

10

L.Ö

, 0

man 12th

o.o

(Broau »)

SSaSi. laria

100

100

100

100

LOO

60

Stel

media)

iOTT

1Ό0

100

30th

v «na fatura;

DEAD

ο Barnyar

«Ö Fortail

7 # lv »t-l ·

Eohlnchlo «crusgalli) Guru »pratansis

Ipoiioeal uVllon IHo

ΪΟΧΓ

10

100

20th

LL

BO

7O

nalepens ·)

100

1OO

■ Sr 80

avloular

100

100

urtas

100

100

100

1OO

LOO

100

Cur;

dock ⁱ fuwex orlspus

1.QU

Crabgra »(Digitaria« anguinalia)

100

100

100

cn co NJ

Tab !! (continuation)

Bar

vroindunn Mr. poeie kg

n s: Mt

/ Sm

Untsuehts Pf lttnson

_ * Thu

Bro— (Bronns)

Of I

Wiieomt * (Awrn

t-bu

ti-Btt
P * Opfl

»6

8.8

e tKotilnchlo cruagtull

Horning

1 (A! Op «cun» i prmfr g glory cipoao ··) • »! • mf Ubutllon In

oanun

ro Johnson

dock

Crabgra «» (D

thmex he ltpm

yLtarla

«Anguina

Hs)

90

t-bu

oyelopropy! -

8.8

BO

80

S-Btt

16

100

100

10

iocr

ϊοο

t-bag
Bt

100

100

100

TOO

1OO

100

100

Τ0 (Γ

100

TOtT

S-BU

1-pr

578 "

100

100

100

100

100

100

100

100

100

100

100

S-Bu S-BiI

8.8

100

100

100

100

1OO

100

100

100

100

100

100

Ι «.

• ion

• ι.

w «4»

P D i>

Sh t- 9>

ΙΛΟ

3S3

109822/2279

Table II

co OO (VS

Pn »

Herbicidal Activity and Selectivity ; from 10 link ϊ ι en of the formula - 17th VI 18 ' 19th 21 Connection no. 2 0 ■ fr t i
ρ b 20th J7W0X KB / UmL
examined priansen 0 100 80 15th 30th 85 O Pigweed (Folygonum avieulare) If 95 100 ¹ TO " 35 - - - - Foxtail (Alopeourus prateneis) 95 90 - 70 45 25th 10 10 0 0 Point 15th 0 30th 100 10 0 80 100 100 25th Crabgrass (Digitaria eanguinalis) 100 100 100 85 100 - 30th 70 45 0 Curled Dock (Rumex crispus) 15th 25th 45 20th 0 0 0 20th 10 0 Corn 20th 30th 20th 30th 20th 45 0 0 0 0 Velvetleaf (Abutilon incanum) 0 0 0 100 0 - - ■ - - - Johnson grass (Sorghum halepense) 45 15th - 0 45 0 0 0 0 0 Soybeans 0 10 0 100 0 0 80 100 100 30th Barnyardgrass (Echinchloe crusgalli) 45 25th 100 45 45 100 - - - - Lambsquarter (Atrlplex) 90 - 20th 0 80 0 0 0 0 Sugar beet 20th 20th 0 - 0 15th 10 0 Alfalfa (Medieago satlva) 0 15th 100 0 95 90 100 100 45 Autumn panum 0 100 80 25th 70 85 100 0 Cheatgrass (Bromue seoalinus) 0 100 0 0 0 - cotton - - 100 0 - 95 100 100 80 Alopecurus mm 100 95 90 0 - _ Chickweed (Stellaria aedia) - - 0 0 - 0 0 0 0 Cucumber 0 0 0 LOO MB Muskaelon (Cucumis melo) - 40 0 85 0 20th 0 0 Morning glory (Ipomoea) 0 10 0 0 - _ Wild mustard - 40 0 100 100 100 70 rice 100 90 15th 0 90 100 100 30th year-round rye 100 0 30th 15th 0 0 - 0 Cocklebur (Xanthium) - - 40 - -> Y.Nutsedge 20th 0 0 0 0 0 0 tomatoes 0 20th 0 0 0 25th 20th 0 Onions 95 - 0 35 100 100 35 Giant Foxtail 100 - - 0 10 0 0 Black nightshade 0 - _ 0 0 0 0 Jinson 0 -

OO N) O

OOOOOO

o4 mo ο ο ι ο

ψΛ CMrI rl

moopοο

CM <M Ο

OOOO 1 IA CM

oooooo

CM

I I i I I I I I I I I I

' 8th

I I I I I I

109822/2279

selectivity Soybeans Tabel III 0 30th Sugar beet Ourken kg / ha 0 of connections 0 20th 0 0 link
No. 1.1 0 0 20th 20th 0 2 1.1 0 0 20th 20th 0 3 1.1 0 ι of the formula VI 0 20th 0 0 5 2.2 0 Tomato cotton corn 0 0 0 0 6th 1.1 0 0 0 20th 0 0 9 1.1 0 0 0 0 0 0 17th 1.1 0 20th 0 0 0 18th 1.1 0 0 - 0 0 0 19th ¹ 1.1 0 0 0 0 0 0 21 1.1 0 0 - 0 0 0 7th M. 0 0 0 0 0 0 10 1.1 0 D. - 0 0 0 11 2.2 0 C. 0 0 14th 1.1 0 16 0 0 0 0,

_ D ₃ -

The following investigations were actually made with use. dung clay * -t «rt.-butyl-N-fcee.-butyl) -2,6-dinitroaniline ("the connection") carried out.

Selectivity of the connection in the Peldtest

An introduction with the help of a cultivator was used for a field teat (Tillrovators) with a double introduction using a disc harrow compared. The treatment was carried out by spraying at the beginning of August at a dose of 160 liters / ha. The connection was placed 5 cm deep with the help of a motor-driven Tillrovator, whereupon 10 grooved flanks and also 4 types of weeds planted the next day and examined 1 month later, at the beginning of September, with regard to the effect of the agent became. The soil was dry on the surface and 5 cm of "rain" fell during the first 3 weeks after the Treatment (2.5 cm of rain and 2.5 cm of irrigation water 2 days after treatment.

Table IV

Reaction of various MutsDflansen and Weed species Treatment (kg / ha 1.1) Tillrovator (Cultivator) Cotton (DPI, soft-leaved) 0 Soybeans (Lee) 0 Peas (qrowder) 0 Cantalope 0 Qurks 0 Beans 0 Johnson grass (Sorghum balepense) 100 Crabgrass (Digitaria sanguinalis) 100 Braohiaria 100 Morning glory (Ipomoea) 75 Coffee herb 80

10982 7/2279

The effect of the compound on the growth of cotton, melons. Tomatoes and cucumber

The plants were grown in plastic pots in the greenhouse, each pot was present 5 times. After spraying, the active ingredient was thoroughly mixed with the aid of a mechanical mixer mixed into the ground. The seed was 1.25 times deep used. The soil used can be called heavy soil be classified.

The sprayer was fitted with an 8002-T-DUse and gave 38Q Liters / ha of spray solution. The treated T. ^ pfe were from watered down to avoid a loss of active ingredient through washing out see below.

The investigation was carried out in 2 phases. Part of the treated soil was immediately planted and a second Part was left to stand in the sun and only after 3 weeks planted.

The growth stimulation was determined by comparison with the same grooved walls on untreated soil. The results are given in Table V in Outer Percentage, the Control Plants being rated at 100 % .

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20582Ü1

Table V

Dose applied immediately before ordering

after the brazen hand.

Order 3 weeks after treatment

Groove »plant

kg / ha

Plant height
in % of the reference plants
29 days after
the treatment

Plant height 48 days after treatment and 27 days after ordering

Melons 0.825 Melons l, f> 5 Cucumber 0.825 Qurks 1.65 tomatoes 0.825 tomatoes 1.65 cotton 0.825 cotton 1.65 untreated 0

118
110
124
128
137
126
118
124
100

114 114

129 104 160 156 147 138 100

Influence of the compound on beans (Henderson baby lima - beans) 1.1 kg / h »4-tert-butyl-N- (sec-butyl) -2,6-dinitroaniline in the form of an» active emulsifiable concentration of 0, 48 kg / liter was applied after dilution before tilling in an amount of 280 liters / ha. The connection was placed 8.7 cm deep twice. The standard dose of trifluralin (0.55 kg / ha) was used for comparison. The beans were harvested in mid-September. The results are summarized in Table VI below.

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Table VI Yield of beans

Treatment Yield per area 45.4 kg bags / ha Increase in yield in I

link

(l, lkg / ha) 463 kg 31.4 25.6

Trifluralin

(0.55 kg / ha) 368 kg 25.0

Effect of the compound on soybeans (Bragg)

The compound was introduced into sandy loam soil at a dose of 1.65 kg / ha in mid-May before the cultivation. I was compared to the age of Chloraahen as a pre-emergence herbicide carried out at a dose of 2.75 kg / ha.

On the test surface it was observed that stronger and stronger plants were produced than on the untreated Verleiohsboden and the ait Chloraaben treated Floor. The suppression of the weed watch gymnastics was on The test surface and the surface treated with chlorine were excellent, but unsatisfactory on the untreated surface. The competition with the weeds pushed back the growth on the untreated area. When chloramben acts see, inter alia, a standard herbicide, the effectiveness of which is that of the Connection was the same. No damage was observed due to this treatment.

109822/2279

Later in the season there was one on the trial area. Significant increase in plant growth and the stem diameter was determined in this Zueamaenhang. The results obtained are summarized in Table VII, The Pods
were harvested from 10 average plants, which were selected from 20 randomly selected plants.

Table VII Soybean stem diameter in cm after treatment with the link Sample No. Compound Standard (untreated)

1 l.i 0.78

2 1.0 0.68

3 1.25 0.90 * 1.1 0.75

5 1.3 0.80

6 1.2 0.52

7 1.25 0.60

8 1.2 0.95

9 1.3 0.50

1.25 0.80

1.4 0.80

:., 1.25 0.60

Oesaatduruhsohnitt 11.60
.1.21 0.6 (p
0.723 Durchaessersunahae in cn Diameter increase in %
of standard 67.4 -

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2058ZÜ7

The increase in yield results from Table VIII,

Table VIII Soybean yield after treatment with the compound

Treatment total yield in kg

Yield increase Yield increase in kg in t

Connection 2.95 standard 0.96

1.99

205.8

The effect of the compound on French beans The compound was introduced in mid-May with the help of an orabstitch cultivator and subsequent harrow treatment and with a whale mulcher within 45 minutes. An area treated with trifluralin was used as a comparison and an untreated area served as a standard. The results obtained are summarized in Table IX below.

Dose kg / ha

Table IX

% Suppression of Breoh Bean Yield / Field (kg) Pigweed Setaria I 11 * total % of the un-

traded Ver gleiohafeldes

veroinaung

<l »i> 90

(1.65) 96

<3.3> 98

Trifluralin

(0.825) 100

100

100

6.89 6.03 12.92 125

7.16
6.62

6.08
6.77

13.24 13.39

128 129

5.20 5.31 10.51 103

Bean yield from two 4.50 m long rows.

Sample areas from a four-foot row within each Test area.

10982 7/7279

- ■ * 9 -

Effect of the compound on cotton

Test A

The compound was applied at a dose of 3.3 kg / ha in late April. Two days later the area was cultivated with cotton of the species OPL. The vegetative growth of the cotton was increased by 3 »3 kg / ha due to the treatment. It was observed that when the cotton reached a height of 37 * 5 cm, the growth was increased by 10 to 50 %. The increase in Waohsturns was not only in the height of the plants, but also in the latitude.

Test B

The compound was applied at a dose of 2.2 kg / ha in mid-April. The order for cotton (Art DPL) was placed 2 days later. The compound was compared with an untreated comparison area and with an area treated with 0.825 kg / ha trifluralin. Treatment with the compound resulted in an increase in plant growth and made the plants generally more robust. 1 independent observers agreed that the area treated with the compound was in contrast to the untreated area and the area treated with trifluralin. The increase in plant growth on the fly treated with the compound was 15 to 20 % compared to the untreated area and the area treated with trifluralin.

109822/2279

The compound was applied at a dose of 2.2 kg / ha in mid-May. The order for old cotton was placed aa the next day. The compound was compared to an untreated area. In the beginning, a delay in the growth of the root across the length of the building wool was observed on the flies treated with the old compound. When the comparative plants in Durchealjiitt had reached a height of 90 cm, the plants treated with the compound had, however, a height of 120 to 135 approx. At this point in time, the development stage of the roots in the building wool plants treated with the old compound was excellent. The increase in ia Wurselwaehstua indicated a stiaulation of the roots with decreasing Xonsentration at the connection through microorganisms (typical reaction to plant regulators). The increase in the plant size in the treated plants, among others 33.3 to 50 t compared to the comparison plants, can be seen in part on the competition for weeds, but based on expert statements, the weed density alone cannot be held responsible for the difference.

109822/2279

Potato Yield Attempts

Before the order was placed, the compound was applied at a dose of 1.65 kg / h to areas of 3 x 12 m, which were each planted with H rows of potatoes. The onkraut suppression was excellent. The yield values are based on three identical samples and on comparison values for each treatment. The potatoes from all areas were sorted into commercial classes (No. 1 and B) and selection. The increase in the amount of marketable potatoes (class B) after treatment with the compound is given as a percentage of the comparison plugs and represents a noticeable increase compared with that with a standard treatment with 0.55 kg / ha trifluralin and 2.2 kg / ha EPTC (S-Xthyldipropylthiocarbanate) are achievable results. The results obtained are summarized in Table X below.

dose Table X class B
159 treatment (1.65) 128 link ♦ BPTC
(0.55 ♦ (kg / ha) Potato yield of
Commercial class in % of comparison Trifluralin Untreated Ver
equal to O number 1
169 2.2) 169

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20582Ö1

Grooving flans selectivity and weed killing compared with the aid of the compound «u trifluralin

The active ingredient was sprayed onto the floor and worked into it. After sowing, the results were 4 weeks determined later; they are in the following table XI in prosentual thinning of weed growth and in percentage Damage to the grove plants indicated.

109827/2279

Active ingredient Dosia
kg / ha Tabel XI [* amb8-
[uarter
Atriplex) 'igweed
Cheno-
podium) Qrae Carpet
Weed
(Mollugo
verticil
.lata) • ure lane
Portulaca
aleraoea) No. link 1.5 soy
beans Cucumber 99 99 100 100 100 1 Trifluralin 1.5
(1.65) 0 0 99 100 100 100 100 link 0 100 99 99 100 100 100 2 Trifluralin 1.5
(1.65) 0 25th 100 100 100 100 100 link 1.5
(1.65) 0 100 95 95 100 100 100 3 Trifluralin 0 0 99 100 100 100 100 0 55 Toma
th 0 40 0 40 0 0

CO N) O

- 51 -

Weed kill and selectivity to alfalft when compared to the compound eu trifluralin

In the Aue Tonleb, sown areas were created, and that was done Treatments using the compressed air method in mid-shark and sun protection of alfalfa seedlings in early June. The state the floor was superb. Two matching Piaches of about 150 m were treated with Ί1Ο liters / ha and irrigated, the treatment being carried out before the planting with alfalfa. The active ingredients used in these experiments and the dosages used were as follows:

Active ingredient

BPTC

Compound Trifluralin Nitralin Compound ♦ BPTC

The existing weed species were Amaranthus retroflexus, Chenopodium album, Koehia, Solanum rostratum, Helianthus echinochloa and Setaria.

The BPTC, the trifluralin and the compound were removed by double disc harrowing and inverted harrowing within 1 hour placed after the application, the depth being approximately 6.2 em, while the other treatments only before the order by double digging. The spray conditions were good.

109822/2279 *

Dose in kg / ha (3.3) (i.i) (0.825) (1.1) (1,1 «■ 2 , 2).

The alfalfa was well tolerated by the Compound at the highest dose of 2.2 kg / ha. The doses of 1.1 and 0.55 kg / ha produced excellent results Control against broad-leaved weed species and grasses, where sufficient control was achieved at 1.1 kg / ha.

Trifluralin at a dosage of 0.825 kg / ha resulted in one very satisfactory weed control, but also led to a noticeable weakening of the stamina and of the guard of alfalfa.

Selectivity of the compound towards grooved flans compared with trifluralin

In the case of a «Herbisid selection process that includes many grooves,

suoh in Hawaii was also the compound when brought in before

the order examined. This test grit took place on the dry side of Kawai Island on a “sandy bottom

With H% organic ingredients instead. 12.5 cm of rain fell

during the early stages of the experiment; an irrigation did not take place. The results obtained are as follows

Table XIZ combined with untreated comparative samples the calculation were taken as a basis.

109822/2279

Tabel XII Trifluralin O likereduk- % Growth link Growth 0 tion reduction % Standing reduction O 0 roögenreduk- in % 0 0 20th tion O 0 20th alfalfa 0 O 0 20th three-leaved Clover O 10 0 20th red clover O 0 20th 20th white clover O 0 0 30th Rape O 20th 50 30th spinach O 0 90 50 tomatoes O 0 30th 90 rice O 0 30th 70 Sugar beet 0 O 30th 30th oats 10 O 30th 20th rye 0 0 30th 30th barley 0 20th 50 peas 0 0 30th Peldaais 0 20th sunflowers O potatoes 0

Studies with the compound and trifluralin on potatoes to compare the herbicidal effectiveness and the selectivity P (Ir the study served Irish willow potatoes (cobblers) in two rows with a distance of 75 cm, the order being made in mid-May with a "farmer". The weed species available for the determination were pigweed (Amaranthus retroflexus), lamb's quarter (Chenopodium album), ragweed (Ambrosia arteraisiifolia), barnyard grass (Bchinoehloe crusgalli) and giant foxtail (Setaria faberii).

10982

The planting bed was treated with a disc harrow three times and rolled twice before ordering. Before the last drive with the disc harrow, 552 kg / ha of a standard fertilizer with 10 % nitrogen, 20 % phosphorus and 20 % potassium (10-20-20) were applied.

The test chemicals were applied earlier on the same day with an improved "bicycle sprayer" (using four 8003 nozzles 45.7 cm apart with a spray height of also 45.7 cm, a pressure of 9.07 kg and a dose of 378 liters / ha). They were then incorporated with the motorized cultivator. The results can be found in Table XIII, the percentages relating to the untreated comparison sample.

• Damage
supply Tabel XIII Lamb's
quarter Pig
weed Rag
weed dose
(kg / ha) Potato
rock 85
87 93
95 0
0 Active ingredient (0.825)
(0.825) 0
23 Giants-
foxtail Connect
manure
Triflu
ralin 95
95 Weed control Barn
yard
grass 95
95

109822/2279

The compound was as active as trifluralin at the same dose. However, trifluralin caused a growth retardation of 23 % in the potatoes at the dose of 0.825 kg / ha, while the compound was completely selective up to a dose of 1.65 kg / ha.

Comparative tests on cereals with the compound versus trifluralin

Summer sages (Selkirk), barley (Erie) and oats (Clintland 60) were sown on a clay soil and treated with the compounds to be investigated at the end of May. Avena fatua, Alopecurus myosuroides and Lolium multiflurum were sown in rows. The Versuohsfläohen were on the following day from above with Watered 0.84 cm of water and before the determination in mid-July another 1 * cm of rain fell.

At the dosages required for optimal weed killing, the damage to the grain was too great; at Pre-emergence use was trifluralin twice as active as that Connection and two to three times as active if it was brought in before the order. The results are in the Table XIV summarized.

109822/2279

Table XIV

dose
(kg / ha) Qerste oats Plant destruction year round
Rossen wilder
oats treatment (0.825)
(0.825) 0
100 0
100; Alopeourus
Sp. 0
90 65
100 link
Trifluralin 70
100

Comparison with rice and the compound in comparison with trifluralin

The rice field was treated with a cultivator and before the order was placed ait rice (Nova 66) was milled, after which the herbicide treatment took place at the beginning of July and was then placed under water. Barnyardgrass was on the Pläehe wide g of · * _r AAET through irrigation and rain beginning and the middle of July kaaen total susasaen 28 s water. The determinations took place in mid-August. The selectivity of the compound was good; the damage by trifluralin at a dose of 0.55 kg / ha was $ 70. The results are given in Table XV below.

Table IV
Active ingredient

link
Trifluralin

Dose <kg / ha)

(0.55) (0.55)

rice

16
70

Plant destruction

broad-leaved weeds

80 100

Barnyard grass

83 96

10982 7/2279

Comparative field tests with the compound and known dinletroaniline herbicides

These HerbisidfeXdversuche were carried out in Santa Isabel. The type of soil varied between gravelly loam and gravelly clay loam; all trial fields were laid out three times. The results are shown in Table XVI below. Planavin is MMethylsulfonic acid) -2,6-dinitro-N, N-dipropylaniline. The treatments were carried out in early January, while the determinations were carried out in mid-February. During this time, the test areas received about 11 cm of water through rain and irrigation.

10982 7/2279

Table XYI treatment

Compound compound compound trifluralin

Trifluralin Tpifluralin

Planavin Planavin Planavin

toaia Ourken Corn soy Rye- tree Toma wheat Barn- Pig Morning coffee (lcg / ha) beans grass wool th yard- weed glory herb sraaa (0.825) 0 0 0 97 0 0 40 73 77 0 0 (1.65) 0 33 0 97 7th 20th 33 77 100 63 0 (3.3) 0 50 10 97 0 47 83 97 97 67 0 (0.55) 40 10 17th 93 33 23 70 93 97 0 0 (0.825) 43 33 33 100 0 40 83 93 97 10 7th (1.65) 37 37 27 100 30th 77 93 97 100 37 17th (0.55) 27 27 3 57 0 7th 60 60 63 63 0 (0.825) 10 33 10 97 7th 10 93 90 97 10 7th (1.65) 20th 17th 30th 77 13th 27 97 93 100 37 27

Pure lane

97 97 93

93 97

100 67 97

IQO

O \ M »

I ■

O CJI00 Ni CD

More attempts at Peldvrgleioha

At a dose of 1.1 kg / ha, the compound was active against annual Qras species, Pigweed (Chenopodium) and Purslane (Portulaea oleraoea). The results are contained in % destruction in Table XVII below.

109822/2279

Table XVII

ο co

ro IN)

treatment dose
(kg / ha) Qurks Corn soy
beans Rye-
grass tree
wool Toma
th Point Barn
yard
grass Pig
weed Purslane link (1.1) 0 0 0. 87 0 7th 47 100 87 93 Trifluralin (1.1) 57 90 0 100 67 73 100 100 93 93 Planavin
(Nitraline) (1.1) 7th 80 0 100 0 73 100 100 77

IS) PO

OV

co

NJ O cn

with corn

Pigweed, Lambsquarter and Barnyardgrass were before the

with

last treatment of the disc harrow sown area-wise. May (Agway 800 Hybrid) was sown and treated in mid-August. The moisture below the surface was sufficient. Before the evaluation, the test areas were given middle September 11 cm of rain and watering.

At a dose of 2.2 kg / ha the compound gave a 90 year old Destruction of Pigweed and Lambsquarter and a £ 100 Destruction of barnyard grass if it is mutually compatible with the grooved plants; Trifluralin and nitraline on the other hand reduced the Maia height by 20 b «w. 10 yrs. The connection was active at the same doses as trifluralin and nitralin, but the damage to the Mals was substantial less. The results are shown in Table XVIII.

dose
(kg / ha) Table XVIII % Plant destruction Lambs
quarter Barnyard
Awesome (2.2) Pigweed 90 100 Active ingredient (2.2) Corn 90 85 100 link (2.2) 0 90 95 100 Trifluralin 20th 90 Nitraline 10

109827/2279

- 65 -

Pre-emergence treatment of crabgrass with a granular preparation of the compound

In early spring, the test area was covered with a cultivator loosened up and seeded with both soft and hairy crabgraes. All treatments were carried out in mid-May, with a lawn beauty spreader with attached drive vibrator ensured uniform application. Using this device, the area was driven at least four times, to apply the active ingredient to areas of 1.20 mx 3.60 m. The area actually treated was 90 3.60 m groft. On the day of application, 0.01 cm of rain fell on the area; the first significant rain (1.52 cm) fell 5 days after the treatment. The results are in the following Table XXX contain.

109822/2279

-3
vjO

Active ingredient dose At #% n A % Table XIX clipping 0 0 I. r "" ¹ * III 0 0 By Beginning SeptetabjerJ III By (kg / ha) ft «^ Crabg DureK- 0 0 60 ■ 40 0 0 cut 10 cut Ver I. cut 0 90 II 70 0 0 I. II 60 search link (1.1) 80 II 0 0 100 80 100 0 ♦ R 60 35 40 95 28 link (2.2) 97 100 in 85 100 75 100 78 70 85 98 72 1 link (4.4) 100 95 75 96 100 - t damage; 100 98 100 98 2 link (8.8) 100 100 95 100 100 0 100 100 100 0 99 3 100 100 100 0 0 * link (1.1) 0 100 B Turf-Toleran «· 0 0 0 0 0 0 link (2.2) 0 0 0 0 0 0 0 0 1 link (4.4) 0 0 0 0 0 0 2 link (8.8) 0 0 * R 0 0 0 3 0 ή

ο cn oo

The compounds according to the invention also show aquatic herbicidal effectiveness, such as the following trial * results prove.

Experiments to control aquatic weeds A container with aquatic weed species in water was treated by adding the active ingredient to be investigated, dissolved in a suitable solvent, at a dose such that the final concentration, as indicated, was 5 or 10 ppm. The effect on the weeds was recorded approximately 3 weeks after the introduction. The results can be found in Table XX.

Table XX Connection conentration in pp "

10 5 5 5 5 5

10

5 5 5 5

100 I annihilation 80 Salvinia duckweed 70 90 100 80 60 50 100 100 60 90 70 100 60 50 30th 0 100 30th 90 0 30th 70 100 90 90 30th

The effect of other compounds according to the invention on inhibition of tobacco sprouts results from the following field tests.

109822/2279

Wachatuasreguliermng for tobacco

Tobacco plants (Pennbel) were cut with a mechanical in mid-June Planting equipment transplanted into the field. 2 months later, in mid-August, they were treated with the compounds to be examined, immediately after the plants have been removed by hand to the first 15 »2cm broad leaves decapitated and of sprouts more than 2.54 cm Length had been released. The plants had just started to bloom.

The plants received from above immediately after spraying an irrigation of 1.27 cn as well as for the duration of the test a total of 40 ca irrigation and rain. Determining the results took place at the end of September.

Excellent tobacco sprout suppression has been achieved Ί-tert-butyl-N- {sec-butyl) -2,6-dinitroaniline ♦ Triton X-100 (an anionic surfactant) at a dose of 2.2 kg / ha + 0.1 % achieved; the control corresponded to that of MH-30 (maleic hydrazide) at a dose of 3.3 kg / ha. Increasing the spray volume from 945 to 1,417 liters / ha with 4-tert-butyl-N- (sec-butyl) -2,6-dinitroaniline alone improved the control of the sprouts. 4 ~ tert-butyl-N- (secbutyl) -2,6-dinitroaniline * 1-decanol «Triton X-100 in a dose of 1.1 kg / ha ♦ 1 J ♦ 0.1 ί was compared to 4-tert .-Butyl-N- (seo.-butyl) -2,6-dinitroaniline alone at a dose of

8 ?? / ?? 79

1.1 or 2.2 kg / ha superior. Alone, 1-Deeanol ♦ Triton X-100 in a dose of 1 to 2 % * 0.1 % had no effect on the growth of the offspring. None of the treatments resulted in any harm. The results can be found in Tables 21 and 22. The "suppression ^{11" is given} as the number of sprouts more than 10 en in length, while the "reduction" means the length of the sprouts on the plants.

109822/2279

Tabel Active ingredient dose
(kg / ha) XXI 10 XXII % Reduction
fcinn 55 gUnder- XReduk- dose
(kg / ha) 93 !Under-
djüüekunit 945 Liffer / ha)
, 1 * Triton X-100
100 gpa 98 1% Deeam
X-100 ♦ i he / ha)
> 1 ♦ Ojlff
LOO gpa Active ingredient 4-tert-butyl-N- 6th
♦ 4-tert-butyl-N- (see-butyl) -2,6- (1.1) (see-butyl) -2,6- (1.1) dinitroaniline % Suppression ifff reduction
(1417 liters / ha) 65 78 73 dinitroaniline (2.2) (2.2) 98 - - η Tabel 15th 60

109822/2279

- 71 -

The preparation of the compounds according to the invention is intended to be explained in greater detail on the basis of the following examples. In particular the preferred starting compounds, reaction conditions and working methods can be found in the examples will"

Example 1 Preparation of 4-tert-butyl-N- (sec-butyl) - 2,6 -dinitroaniline

Stage A Production of 4-tert-buty1-2,6-dinitrophenol

According to the method of Dutton et al (Canadian Journal of Chemistry 21 » ⁶⁸ 5 (1953)) 200 g (1.32 Hol) 4-tert-butylphenol were dissolved in H 80 al glacial acetic acid and the solution was added dropwise over the course of 1 hour Rahren su a solution of 320 al 90 * nitric acid in 600 ml glacial acetic acid at -10 to -15 ⁰ C sugefOgt "After completion of the addition the temperature rose to O to to -5 ° C and then the reaction mixture was allowed to stand ·, so when it reached room temperature. The mixture was held at this temperature for 1 hour, then poured onto crushed ice, diluted with water and cooled. The product was filtered off, washed with water, dried and recrystallized from hot hexane, 180 g of 4-tert-buty1-2,6-dinitrophenol being obtained in the form of fine yellow needles with a skin point of 9 ° to 95 ° C.

10982 7/2279

8tufe B Production of * -tert-butyl-2,6-dinitrochlor bensol

180 g (0.75 mol) * -tert-butyl-2,6-dinitrophenol were in a mixture of 113 g (0.95 mol) thionyl chloride, 55 g (0.76 mol) dimethylformamide and 300 ml dry toluene given. The mixture was stirred and refluxed for 15 hours, after which the thionyl chloride, DMF and toluene were suctioned off under reduced pressure until a slurry remained. Hexane was then added to the reaction vessel, whereupon the qeaiach was cooled and filtered off. Subsequently, the product was recrystallized from boiling hexane to give 168 g of ^J l-tert-butyl-2,6-dinitrochlorbenEol were obtained in the form of pale yellow needles of melting point U4 to IL6 ° c.

Stage C Production of ft-tert. ~ Butyl-N- (sec.-butyD-

2,6-dinitroaniline

1 g of tert-butyl 1-2,6-dini.trochlorbensol was unset with 1 g of sea-butylamine by adding the amine dropwise to a refluxing mixture of 50 ml of dry toluene and M-tert-butylamine. 2,6-dinitrochlorobenzene was added. After the addition was complete, the mixture was refluxed for 8 hours. It was then cooled to room temperature and the amine hydrochloride was filtered off.

109822/2279

ir ^: ""'\ ■ -'"; ■■ * ■■. -"; ■ ""; ^! '-' ■■■. ■■; ; ■ ■ ■ ■ V-; ■ ■ ■ ■ ■■■

- 73 -

The toluene and the unreacted amine were removed from the reaction mixture under reduced pressure and the remaining thick material was dissolved in hot ethanol. It crystallized on cooling to give 4-tert-butyl ~ N ~ (eee.-butyl) -2,6 ~ dinitroaniline was obtained with melting point 60 to 62 ⁰ C.

Example 2 Preparation of H-tert-butyl-N-methyl-2,6-

dinitroaniline

2.6 g (0.01 mol) of 4-tert-butyl-2,6-dinitroohlorbensol were reacted with 3 »1 g of a HO aqueous solution of methylamine in 50 μl of ethanol. The temperature was as follows slowly increased: 30 ⁰ C for 1 hour, 40 ° C for 1 hour, long 50 ⁰ C for 1 hour and 80 ⁰ C for 5 hours · After completion of the Umsetsung were added about 100 ml of water to give the product has been filled out. The same was filtered off, washed with several portions of water, and after recrystallization from ethanol, 2.5 g of tert-Buty1-Ί-N-raethy1-2,6-dinitroanilln in the form of orange-colored needles melting at 129-130 ⁰ C obtained.

10982 2/227 9

Example 3 Preparation of 4 "tert-butyl-N-ethyl-2 _s 6- dinitroaniline

Following the procedure of Example 2, 2 g of a 70 * igen were obtained aqueous solution of ethylamine with 2.6 g (0.01 mol) of 4-tert-butyl-2,6-dinitrochlorobenzene su 2 g of 4-tert-butyl-N ~ ethyl-2,6-dinitroaniline implemented in Porm of orange colored needles with a melting point of 70 to 73 ° C.

Example 4 Preparation of 4-tert-butyl-N- (see.butyl) -2,6- dinitroaniline _

Level a

1.5 g (0.11 mol) of sodium hydroxide was dissolved in 100 ml of methanol, and 32.4 g (0.10 mol) of 4-tert-butyl-2,6-dinitrophenol was dissolved in the resulting solution. 23 g (0.12 mol) of tosyl chloride was added to the liquid and the demise was stirred at 35 ° C for 1.5 hours. The Peststoff formed was filtered off and washed with water to give 33 g (84 t yield) of light yellow tosylate, melting point 124-130 ⁰ C were obtained.

Level B.

29.4 g (0.10 mol) of the tosylate and 14.6 g (0.20 mol) sec-butylanine in 200 ml of water were stirred together and 3 hours heated to the smoke air temperature for a long time. After cooling down

109822/2279

2Q58201

- 75 -

At room temperature the mixture was filtered and the formed pesticide was washed with water. The dried product, ty-tert-butyl-N ~ (see-butyl) ~ 2,6-dinitroaniline, weighed 23.6 g (80 % yield).

Example 5 An emulsifiable concentrate (2.2 kg / ha) The following substances were added together and stirred until

see a homogeneous solution had formed.

Component kg Qew *

4-tert-butyl-N- (see-butyl) -
2,6-dinitroaniline 0.916 23, ^ 0 Atlox 3387 (an anionic
Net «medium) 0, W 11.59 Panasol AN-3
(an aromatic solvent) 2.5 * 0 65.01

3.91 100.00 The specific weight at 20 ° C was 1.037.

Example 6 A granular preparation

4.2 parts by weight of 4-tert-butyl-N- (see-butyl) -2,6-dinitroaniline were dissolved in 15.0 parts of acetone and the solution was stirred into 95.8 parts by weight of vermiculite (Trenton No. H ) sprayed on. Subsequently, the solvent was evaporated.

109827/2279

Example 7 A Consistent Solution

The following ingredients have been mixed up until they become a solution had formed and the correct specific gravity of 1.010 was reached at 20 ° C.

Component kg Qew *

4-tert-butyl-N- (acc-butyl) -

2,6-dinitroaniline 1.911 50.48

Toximul D (a mixture of

an anionisehen and a «

non-ionic emulsifier) 0.191 5.00

Dimethylformamide 0.453 11.88

Xylene (0.868 at 20 ⁰ C) 1.245 32.64

3,800 100.00.

10982 2/2279

Claims (1)

I. P ι t β η t «η β ρ r α oh e lytt-Bono-substituted * -butyl-2,6-dinitroaniline der gray fora ·! VX (VI) \ in the Bu a tert-butyl or »eo.-butyl radical and R a j Waeeoretoffato * or an alkyl, cycloalkyl, cyolo- I alkylalkyl, alkenyl, alkynyl, alkoxyalkyl or dialkoxy J mean alkyl radical or its salt «. I · j 2. Dinitroaniline common test 1 »characterized by } that the Atkylreet R is a straight or branched chain I Alkylreet "with 1 to 6 carbon atoms ift. 3. Dinitroaniline according to Claim 2, characterized by / daA the AlJqrlreat R a xeopropyl, mo.-butyl or tert.- I butyl reet iat. . 1 ■ \ ■ ■■ j 109822/2279 - 78 - 4 · Dinitroanlin according to Claim I ₉ characterized by the fact that the cyoloalkyl radical R is monocyclic and contains 3 to 6 carbon atoms. 5. Dinitroaniline according to claim 4, characterized in that because the cycloalkyl residue R "is in cyclohexylr" et. 6 · Dlnitroaollin s ··! ·· Claim 1, thereby k «nn» * ichnet, da * a * r CjreloallqriÄlkylr ·· * R * bia 9 carbon atoms contains. 7 Dinltroaniline aeaiss claim 6, thereby gsksnnsslehiist, that the cyeloalkali metal residue R is a cyolohexylasthyl residue. 8. Dinltroaniline fsaiss Anspnieh 1 «thereby gsksimselehiist, daA the alkenyl radical R is straight or Teriveift chain Alkenjlrest old 3 to 1 is carbon atoms. ' 9 Oinltroanllln amiss claims 8, thereby eekeaniehnet, that the alkenyl ride R «is in allyl chain. lqplnltroanllin genlia Ansprush I ₉ fekennseiohnet that the Alklnylrett R sin straight or offset 3 to% carbon atoms is " 109822/22 * 79 | ir fTiiiini; .. .. ■; _. ■■ « - 79 -. 11 * Dinitroaniline according to claim 10, characterized in that because the alkynyl radical R is a propynylreat. 12. Dinitroaniline according to claim 1, characterized in that the alkoxyalkyl radical R is a radical of the general formula CH, (CH ₂ ) -0- (CH ₂ ) -, where m is 0 or 1 and η is a whole number from 1 to 6 . 13 «Dinitroaniline according to claim 12, characterized in that if the alkoxyalkyl radical R is methoxymethyl, Hethoxyäthyl-, Methoxypropyl, methoxyisopropyl, xthoxymethyl, xthoxyethyl, Xthoxypropyl or Xthoxyisopropyl radical. H. Dinitroaniline according to claim 1, characterized in that the dialkoxyalkyl radical R is a radical of the general formula (CH, (CH ₂ ) _{| R} -O) ₂ -C _n H _2n . _{Is 1} , where m is 0 or 1 and η is 1 to 6. 15 · Dinitroaniline according to claim 14, characterized in that the dialkoxyalkyl radical R is a diaethoxyethyl, diaethoxyethyl, Diaethoxypropyl-, Diaethoxyisopr.opyl-, Diethoxyaethyl-, Diethoxyethyl, diethoxypropyl or diethoxyisopropyl residue is. 10 9822 / 2-279 - 8o - 16. Dlnitroanilln according to claims 1 to 15, characterized characterized in that the Heat Bu is a tert-butyl radical let. 17 dinitroaniline according to claim 16, characterized in that since the radical R is an alkyl radical. Id. Dlnitroanilln according to claim 17 »characterized in that daA the radical Bu a tert-butyl radical and the radical R a is branched-chain alkyl. 19. J-tert -Butyl-N-methyl-1, 6-dinitroaniline. 20. * -t «rt.-Butyl-N-ethyl-2,6-dinitroaniline. 21. J | -tert. -Butyl-N-isopropyl-2,6-dinitroaniline. 22. 4-tert-Butyl-N- (n-butyl) -2,6-dinitroaniline. 23. 4-t «rt.-Buty1-N- < see-butyl) -2, £ -dinitroaniline. 2 *. * -tert-butyl-N- (tert-butyl) -2,6-dinitroaniline. 25. 4-tert-Butyl-N- (tert-pentyl) -2,6-dinitroaniline. 26. ^ -terVButyl-H-isopentyl-Sjß-dinitroaniline. 27. ^ -tert-butyl-N-ally1-2,6-dinitroaniline. 28. 4-tert-Butyl-N- (3 '- «ethoxypropyl) -2,6-dinitroaniline. 29 · * -tert-butyl-N- (2 ·, 2'-diJMthoxyethyl) -2,6-dinitroaniline. 30. 4-tert-butyl-N-cyclohexyl-2,6-dinitroaniline. 31. * -t «rt.-Butyl-M-n-hexyl-2,6-dinitroaniline. 32. * -t «rt.-Buty1-M-oyclopropy1-2,6-dinitroaniline. 109822/2279 COPY J - 8i - 33. 4-tert-Butyl-H- (oyelopropylaethyl) -2,6-dinitroaniline. 3 * · 4-see.-Buty1-H-methy1-2, δ-dinitroaniline. 35 · 4-sec-butyl-N-ethyl-2,6-dinitroaniline. 36. 4-see, -butyl-N-isopropyl-2,6-dinitroaniline. 37. 4-sec, -butyl-N-feec.-toutyl) -2,6-dinitroaniline. 38. 4-see-Buty1-M- (n-buty1) -2,6-dinitroaniline. 39 · 4-sec-butyl-H- (tert-biityl) -2,6-dinitroaniline. 40. 4-seo.-Buty 1-N-eyelohexy 1-2,6-dinitroaniline. - ^ _. 41. 4-eee.-Butyl-ii- (2 ^t , 2 »-dinethoxylth» l) -2,6-dinitroaniline. 42 4-sec.-Buty 1-H- (3 '-swthoxypropy 1) -2,6-dinitroaniline 43 · Process for the preparation of M-monosubstituted substances 4-butyl-2,6-dinitroanilines geo & as claims 1 to 42, characterized in that a corresponding primary Aain of the general formula R NH ₂ , in which R has the meaning given above, with a suitable 4-butyl-2, 6-dinitrophenyl chloride of the general formula Bu- (VII) Cl implement; in which Bu has the meaning given above. 109822/2279 COPY The method grates claim 43, characterized in that ■ an inert organic solvent as reaction medium used. 45.Verfahren according to claim 44, characterized in that «Toluene, xylene or ethanol are used as solvents. 46. The method according to claim 43, characterized in that that nan used an aqueous reaction medium. 47 «Method according to claim 46, characterized in that the aqueous reaction medium is aqueous ethanol. 48. The method according to claims 43 to 47, characterized thereby «Eiohmit that you can use the amine in a molar Use excess. 49.Procedure according to speeches 43 to 48, thereby marked, that the 4-butyl-2,6-dinitrophenylohlorid of the formula VII, which is used as the starting compound durob conversion of a corresponding 4-butyl-2,6-dinitrophenol with a chlorinating agent in the presence of a complexing amide. 109822/2279 * - 83 - 5O.Method according to claim 9, thereby keraiseiohnet, daft ■ as a chlorine release agent thionyl chloride, phosphorus oxychloride or phosphorus penta chloride used 5i.Process according to Aneprachen k 9 or 50, characterized by the fact that formamide, acetamide or propionamide or their alkyl-containing derivatives, such as dinethylforeanide, are used as amides. 52.Verfahren meet claims ¹ 19 to 51, characterized in that the Cblorlerungsaittel and the amide are used in approximately Squlmolar amounts. 53.Verfahren according to claim 52, characterized in that the amide and the chlorinating agent are used in molar quantities uses which of the amount of 4-butyl-2,6-dinitrophenol at least equal or exceed « 5 * .Process according to claims H9 to 53, characterized in that the reaction is carried out in an inert organic solvent. 55 · The method according to claim 5 *, characterized in that daft the solvent used is toluene or xylene. 109822/2279 56. The method according to speeches 49 to 55 »characterized in that that the ümsetsungsteaperatur the Röokfluss Temperatur of the reaction mixture. 57. The method according to claims 49 to 56, characterized in that that one used that as the starting compound 4-tert-butyl-2,6-dinitrophenol of the general formula VIII by entrainment of the corresponding p-butylphenol3 der general form HX, in which Bu has the meaning given above has, represents. 58. The method according to claim 57 · characterized in that nitration is carried out using nitric acid pass through in acetic acid solution. 59 · Vervendung the N-monosubstituted 4-butyl-2,6-dinitroaniline · accordance with the addresses 1 to 42 as Unkrautvertilcuügssdttel and / or Pflansemraehsregulierungsmittel, particularly sur 3ekämpfuns of weed grasses and breitbllttrigen Onkrautarten and sur growth regulating rice _x tobacco, maize, beans, Potatoes, cotton, sorghum tomatoes, asparagus, onions, pumpkin, cereals, peas, ravens, pepper or sunflowers. 109822/7279 _C OPY 60.Use according to claim 59 »characterized in that dad you take the active ingredient before sowing or planting or uses as a pre-emergent agent. 61 «Use according to claims 59 and 60, characterized in that if the active ingredient is used in an amount of 0.28 to 17 * 6 kg / ha, preferably 0.55 to 5.5 kg / ha. 62.Use according to claims 59 to 61, characterized in that then the active ingredient in the form of a liquid, powder or granules susaaaen aa carrier, preferably ait attapulgite, clay, vermiculite, ammonium nitrate, urea, or ground Apples corn on the cob. . 63. Use according to claim 62, characterized in that the preparation contains 2 to 20 Qewf of active ingredient. 64.Use according to claim 62, characterized in that the active ingredient is used in the form of an emulsifiable xon concentrate which, in addition to the active ingredient, contains a water-soluble or water-dispersible organic solvent and optionally one or more solubilizers together as a hardening agent,
coll. 109822/2279